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Results: 945 Rentals

  • Brownstone in Gold Coast
    From $302 per night (USD)

    VRBO

    Brownstone in Gold Coast

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    9

    Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...

    From $302 per night (USD)

    VRBO

    Details
  • Luxury Downtown Penthouse with Private Rooftop!
    From $531 per night (USD)

    Expedia

    Luxury Downtown Penthouse with Private Rooftop!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    10

    Summary: BRAND NEW REMODEL BUILT SPECIFICALLY FOR AIRBNB!! Designed by a famous Chicago Designer using strictly West El ...

    From $531 per night (USD)

    Expedia

    Details
  • The Orleans Floor 3 Private rooftop deck!
    From $1418 per night (USD)

    VRBO

    The Orleans Floor 3 Private rooftop deck!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    16

    Summary: You will get the following with this rental: - You will have your own private floor and access to 2 individual ...

    From $1418 per night (USD)

    VRBO

    Details
  • The Orleans - Floor 2 Private roof deck Patio!
    From $1480 per night (USD)

    Expedia

    The Orleans - Floor 2 Private roof deck Patio!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    16

    Summary: The Orleans - Floor 2 is custom designed for Airbnb and you will get 2 units on an entire floor of the building ...

    From $1480 per night (USD)

    Expedia

    Details
  • Landing at 500 Lake Shore Drive - 1 Bedroom in Streeterville
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    VRBO

    Landing at 500 Lake Shore Drive - 1 Bedroom in Streeterville

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    500 Lake Shore Drive was designed with your lifestyle in mind. Take a dip in the rooftop pool, then retreat from the sun ...

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    VRBO

    Details
  • 858 Orleans
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    Expedia

    858 Orleans

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    11

    <p>While you're here, you can enjoy all the comforts of home and more, including a full-sized refrigerator/freezer and a ...

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    Expedia

    Details
  • Cozy 1-bedroom apartment .luxury building
    From $226 per night (USD)

    VRBO

    Cozy 1-bedroom apartment .luxury building

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This memorable apartment is the perfect home base for your trip to Chicago. Nestled in the heart of the city, this charm ...

    From $226 per night (USD)

    VRBO

    Details
  • Elegant King Bed 1.5 Bath Suite in the Heart of Chicago's Gold Coast
    From $204 per night (USD)

    VRBO

    Elegant King Bed 1.5 Bath Suite in the Heart of Chicago's Gold Coast

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Each apartment offers a luxurious living experience, as they come fully furnished with all the amenities you could need. ...

    From $204 per night (USD)

    VRBO

    Details
  • Elegant 1 Bed Suite at Walton Residence in Gold Coast Chicago
    From $215 per night (USD)

    VRBO

    Elegant 1 Bed Suite at Walton Residence in Gold Coast Chicago

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Each apartment offers a luxurious living experience, as they come fully furnished with all the amenities you could nee ...

    From $215 per night (USD)

    VRBO

    Details
  • 870 bldg - 3 Separate Suites in same building
    From $2514 per night (USD)

    Expedia

    870 bldg - 3 Separate Suites in same building

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    16

    Summary: This listing is ideal for LARGE GROUPS that wish to have individual Suites and separate living spaces for diffe ...

    From $2514 per night (USD)

    Expedia

    Details
  • Downtown Park Mich Ave Penthouse - Rooftop & Gym
    From $281 per night (USD)

    VRBO

    Downtown Park Mich Ave Penthouse - Rooftop & Gym

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...

    From $281 per night (USD)

    VRBO

    Details
  • Chicago Cityview Chic -  Gold Coast/River North
    From $190 per night (USD)

    Expedia

    Chicago Cityview Chic - Gold Coast/River North

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our stylish, modern 2-bed, 1-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover ...

    From $190 per night (USD)

    Expedia

    Details
  • Luxury 2 bed. Views of Navy pier, lakefront and city! Beach within steps!
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    VRBO

    Luxury 2 bed. Views of Navy pier, lakefront and city! Beach within steps!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Clean! Clean! Clean! 39th floor with Amazing views!!! Lots of space. Large Chefs Kitchen for entertaining! Sunrise eve ...

    Click For Pricing

    VRBO

    Details
  • River North Luxury Condo 2 King Beds 2 Baths
    From $214 per night (USD)

    VRBO

    River North Luxury Condo 2 King Beds 2 Baths

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the sought-after neighborhood of River North, this 2/2 high-rise condo provides luxury accommodations with am ...

    From $214 per night (USD)

    VRBO

    Details
  • Downtown Gold Coast 4bd/4ba - 2 apts
    From $968 per night (USD)

    VRBO

    Downtown Gold Coast 4bd/4ba - 2 apts

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...

    From $968 per night (USD)

    VRBO

    Details
  • Luxury Loft Collection 903 - Terrace - River North
    From $768 per night (USD)

    Expedia

    Luxury Loft Collection 903 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    14

    Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...

    From $768 per night (USD)

    Expedia

    Details
  • Luxury Loft Collection 902 - Terrace - River North
    From $759 per night (USD)

    VRBO

    Luxury Loft Collection 902 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    14

    Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...

    From $759 per night (USD)

    VRBO

    Details
  • Luxury Loft Collection COMBO 902/903 Terrace
    From $1519 per night (USD)

    Expedia

    Luxury Loft Collection COMBO 902/903 Terrace

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    30

    Summary: Enjoy the combination of your own 2 side-by-side private luxury lofts in Chicago's bustling River North-the cit ...

    From $1519 per night (USD)

    Expedia

    Details
  • Stellar South Loop 1BR, near CTA Train, Sports & Parks, by blueground
    From $98 per night (USD)

    VRBO

    Stellar South Loop 1BR, near CTA Train, Sports & Parks, by blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...

    From $98 per night (USD)

    VRBO

    Details
  • Stunning South Loop 2BR w/ Doorman, near Aquarium & Train, by Blueground
    From $112 per night (USD)

    Expedia

    Stunning South Loop 2BR w/ Doorman, near Aquarium & Train, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this cozy two bedroom Blueground apartment. You’ll love coming hom ...

    From $112 per night (USD)

    Expedia

    Details
  • Beautiful Unit CHI in Prime River North - 2
    From $519 per night (USD)

    VRBO

    Beautiful Unit CHI in Prime River North - 2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: Downtown Living is perfect for families, children and corporate gatherings. Looking to stay in the best neighbo ...

    From $519 per night (USD)

    VRBO

    Details
  • Historic and Unique Brownstone in Gold Coast - 3
    From $185 per night (USD)

    Expedia

    Historic and Unique Brownstone in Gold Coast - 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...

    From $185 per night (USD)

    Expedia

    Details
  • 2nd Floor Flat in River North - 2N
    From $294 per night (USD)

    VRBO

    2nd Floor Flat in River North - 2N

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    Summary: BRAND NEW REMODEL BUILT SPECIFICALLY FOR AIRBNB. The entire property is designed by a famous Chicago Designe ...

    From $294 per night (USD)

    VRBO

    Details
  • 3rd Floor Flat in River North - 3N
    From $300 per night (USD)

    Expedia

    3rd Floor Flat in River North - 3N

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    Summary: REMODELED AND BUILT SPECIFICALLY FOR AIRBNB. The entire property is designed by a famous Chicago Designer us ...

    From $300 per night (USD)

    Expedia

    Details
  • Beautiful Unit CHI in Prime River North - 1
    From $519 per night (USD)

    VRBO

    Beautiful Unit CHI in Prime River North - 1

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: This is a super unique place! This Downtown Living destination is perfect for everything from families with sma ...

    From $519 per night (USD)

    VRBO

    Details
  • 2nd Floor Flat in River North - 2S
    From $561 per night (USD)

    Expedia

    2nd Floor Flat in River North - 2S

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    10

    Summary: BRAND NEW REMODEL BUILT SPECIFICALLY FOR AIRBNB. Designed by a famous Chicago Designer using strictly West E ...

    From $561 per night (USD)

    Expedia

    Details
  • Striking South Loop 1BR w/ Rooftop, walk to Grant Park, by Blueground
    From $90 per night (USD)

    VRBO

    Striking South Loop 1BR w/ Rooftop, walk to Grant Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...

    From $90 per night (USD)

    VRBO

    Details
  • Sweet South Loop 1BR w/ Rooftop, nr Grant Park & Museums, by Blueground
    From $85 per night (USD)

    Expedia

    Sweet South Loop 1BR w/ Rooftop, nr Grant Park & Museums, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated South Loop furnished one bedroo ...

    From $85 per night (USD)

    Expedia

    Details
  • Sunny South Loop 1BR, nr Soldier Field, CTA Train & Park, by Blueground
    From $122 per night (USD)

    VRBO

    Sunny South Loop 1BR, nr Soldier Field, CTA Train & Park, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in South Loop. It’ll be easy to simply show up and start l ...

    From $122 per night (USD)

    VRBO

    Details
  • #1608 - Kasa Magnificent Mile Chicago
    From $303 per night (USD)

    VRBO

    #1608 - Kasa Magnificent Mile Chicago

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...

    From $303 per night (USD)

    VRBO

    Details
  • Gold Coast/Downtown Hideaway
    From $331 per night (USD)

    VRBO

    Gold Coast/Downtown Hideaway

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    New Listing! Freshly renovated Gold Coast hideaway provides the perfect escape from the nearby shopping and restaurant a ...

    From $331 per night (USD)

    VRBO

    Details
  • Luxury Loft Collection 703 - Terrace - River North
    From $740 per night (USD)

    Expedia

    Luxury Loft Collection 703 - Terrace - River North

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    14

    Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...

    From $740 per night (USD)

    Expedia

    Details
  • Luxury Designer Penthouse West |Pool| Gold Coast
    From $638 per night (USD)

    VRBO

    Luxury Designer Penthouse West |Pool| Gold Coast

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...

    From $638 per night (USD)

    VRBO

    Details
  • Chicago Cityview Chic II Gold Coast/River North
    From $270 per night (USD)

    Expedia

    Chicago Cityview Chic II Gold Coast/River North

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...

    From $270 per night (USD)

    Expedia

    Details
  • South Loop 4 Bedroom apt
    From $319 per night (USD)

    VRBO

    South Loop 4 Bedroom apt

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    9

    Summary: South Loop 4 bedroom apartment with 1.5 bathrooms. We are centrally located and very easy to get anywhere in th ...

    From $319 per night (USD)

    VRBO

    Details
  • Luxury Designer Penthouse Combo |South| Gold Coast
    From $1396 per night (USD)

    VRBO

    Luxury Designer Penthouse Combo |South| Gold Coast

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    20

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...

    From $1396 per night (USD)

    VRBO

    Details
  • Luxury Designer Penthouse Combo |North| Gold Coast
    From $1509 per night (USD)

    VRBO

    Luxury Designer Penthouse Combo |North| Gold Coast

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    20

    Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...

    From $1509 per night (USD)

    VRBO

    Details
  • Downtown Penthouse 5bd VIEWS|Parking, Gym+Pool
    From $1382 per night (USD)

    Expedia

    Downtown Penthouse 5bd VIEWS|Parking, Gym+Pool

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    14

    Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with M ...

    From $1382 per night (USD)

    Expedia

    Details
  • 2 Connecting Suites at a 4⭐️ Hotel
    From $1085 per night (USD)

    VRBO

    2 Connecting Suites at a 4⭐️ Hotel

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Delight in exclusive access to the Club Lounge in the Executive Suite at the Renaissance Chicago Downtown Hotel. This 80 ...

    From $1085 per night (USD)

    VRBO

    Details
  • Discover Downtown from Our Well-Appointed Space | 2 Suites
    From $574 per night (USD)

    VRBO

    Discover Downtown from Our Well-Appointed Space | 2 Suites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    10

    Downtown at Your Doorstep: In the vibrant Loop's heart, our boutique hotel is an urban oasis. Near the Art Institute & M ...

    From $574 per night (USD)

    VRBO

    Details
  • Downtown 9bd - Sleep 18 - (4 units, same floor)
    From $1792 per night (USD)

    VRBO

    Downtown 9bd - Sleep 18 - (4 units, same floor)

    Bedrooms:
    5
    Bathrooms:
    9
    Sleeps:
    16

    Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...

    From $1792 per night (USD)

    VRBO

    Details
  • Downtown 2bd #6 +Gym near Park, Lake, Museums
    From $337 per night (USD)

    Expedia

    Downtown 2bd #6 +Gym near Park, Lake, Museums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...

    From $337 per night (USD)

    Expedia

    Details
  • Downtown 2bd #5 +Gym near Park, Lake, Museums
    From $336 per night (USD)

    VRBO

    Downtown 2bd #5 +Gym near Park, Lake, Museums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...

    From $336 per night (USD)

    VRBO

    Details
  • Downtown 3bd #7 near Park+Museums
    From $452 per night (USD)

    Expedia

    Downtown 3bd #7 near Park+Museums

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...

    From $452 per night (USD)

    Expedia

    Details
  • Downtown 2bd #4 - Near Grant Park, Museums, Lake
    From $345 per night (USD)

    VRBO

    Downtown 2bd #4 - Near Grant Park, Museums, Lake

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...

    From $345 per night (USD)

    VRBO

    Details
  • Group Hub: 3 Designer 2BR, Steps to Mag Mile
    From $2013 per night (USD)

    VRBO

    Group Hub: 3 Designer 2BR, Steps to Mag Mile

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    15

    Summary: For the ultimate Chicago group getaway, consider 'The Mary,' our collection of three modern 2BR apartments perf ...

    From $2013 per night (USD)

    VRBO

    Details
  • Downtown Group Ideal: 2 Luxury Units, Iconic Views
    From $1613 per night (USD)

    VRBO

    Downtown Group Ideal: 2 Luxury Units, Iconic Views

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    15

    Summary: Accommodate your large groups in 'The Apollo', our two high-end apartments in a central location near iconic Ch ...

    From $1613 per night (USD)

    VRBO

    Details
  • Two Units: Seamless Stay, Downtown Convenience
    From $1299 per night (USD)

    VRBO

    Two Units: Seamless Stay, Downtown Convenience

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Your perfect spot for large groups in downtown Chicago! 'The Winfrey' offers two 2BR apartments in the same bui ...

    From $1299 per night (USD)

    VRBO

    Details
  • Gold Coast Group Stay: 2 Modern 2BR Apartments
    From $1235 per night (USD)

    VRBO

    Gold Coast Group Stay: 2 Modern 2BR Apartments

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Plan your Chicago group getaway with our two stylish 2BR apartments in the prime location of the Gold Coast, of ...

    From $1235 per night (USD)

    VRBO

    Details
  • Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground
    From $112 per night (USD)

    Expedia

    Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...

    From $112 per night (USD)

    Expedia

    Details
  • Luxury Downtown PH: Bean & Lake Views
    From $2253 per night (USD)

    VRBO

    Luxury Downtown PH: Bean & Lake Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Chicago's Exclusive Orion Penthouse! Wake to breathtaking Bean & Park views from your 21st-floor, 3000ft² haven ...

    From $2253 per night (USD)

    VRBO

    Details
  • The Lyra: Luxury Group Getaway - Two Penthouses
    From $5094 per night (USD)

    VRBO

    The Lyra: Luxury Group Getaway - Two Penthouses

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    15

    Summary: Discover 'The Lyra', a collection of two exclusive penthouses on the same floor in The Loop, perfectly situated ...

    From $5094 per night (USD)

    VRBO

    Details
  • Blueground | South Loop 1bd apartment
    From $89 per night (USD)

    VRBO

    Blueground | South Loop 1bd apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...

    From $89 per night (USD)

    VRBO

    Details
  • Blueground | River North 2bd apartment
    From $535 per night (USD)

    Expedia

    Blueground | River North 2bd apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished two bedroo ...

    From $535 per night (USD)

    Expedia

    Details
  • Blueground | South Loop 1bd apartment
    From $118 per night (USD)

    VRBO

    Blueground | South Loop 1bd apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...

    From $118 per night (USD)

    VRBO

    Details
  • Blueground | River North 2bd apartment
    From $242 per night (USD)

    Expedia

    Blueground | River North 2bd apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...

    From $242 per night (USD)

    Expedia

    Details
  • Blueground | South Loop 2bd apartment
    From $114 per night (USD)

    VRBO

    Blueground | South Loop 2bd apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in South Loop with high floor views over the city. It’ll b ...

    From $114 per night (USD)

    VRBO

    Details
  • Blocks from the buzz of Magnificent Mile
    From $756 per night (USD)

    Expedia

    Blocks from the buzz of Magnificent Mile

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Chicago is waiting for you at this awesome 1-bedroom hotel. The property offers a cozy bedroom and a relaxing bathroom f ...

    From $756 per night (USD)

    Expedia

    Details
  • Blueground | South Loop, rooftop & gym, nr parks
    From $78 per night (USD)

    VRBO

    Blueground | South Loop, rooftop & gym, nr parks

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this roomy one bedroom Blueground apartment. You’ll love coming ho ...

    From $78 per night (USD)

    VRBO

    Details
  • Blueground | South Loop, rooftop & gym, nr park
    From $139 per night (USD)

    Expedia

    Blueground | South Loop, rooftop & gym, nr park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...

    From $139 per night (USD)

    Expedia

    Details
  • Blueground | Streeterville, pool & gym, nr pier
    From $146 per night (USD)

    VRBO

    Blueground | Streeterville, pool & gym, nr pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this roomy Streeterville furnished one bedroom apa ...

    From $146 per night (USD)

    VRBO

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $203 per night (USD)

    Expedia

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...

    From $203 per night (USD)

    Expedia

    Details
  • Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
    From $284 per night (USD)

    VRBO

    Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $284 per night (USD)

    VRBO

    Details
  • Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units
    From $542 per night (USD)

    VRBO

    Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $542 per night (USD)

    VRBO

    Details
  • 2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park
    From $542 per night (USD)

    VRBO

    2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $542 per night (USD)

    VRBO

    Details
  • Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park
    From $256 per night (USD)

    VRBO

    Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $256 per night (USD)

    VRBO

    Details
  • Elegant Room w/ Modern Conveniences & Walkable to Major Attractions
    From $282 per night (USD)

    VRBO

    Elegant Room w/ Modern Conveniences & Walkable to Major Attractions

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $282 per night (USD)

    VRBO

    Details
  • Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier
    From $282 per night (USD)

    VRBO

    Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in the Loop, steps from The Theatre District and Millennium Park, immerse yourself in Chicago’s marvels. Discove ...

    From $282 per night (USD)

    VRBO

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $176 per night (USD)

    VRBO

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...

    From $176 per night (USD)

    VRBO

    Details
  • Luxury Designer Penthouse|Private Deck|Gold Coast
    From $690 per night (USD)

    VRBO

    Luxury Designer Penthouse|Private Deck|Gold Coast

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Summary: BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's ce ...

    From $690 per night (USD)

    VRBO

    Details
  • Luxury Designer Apartment | Patio | Gold Coast
    From $668 per night (USD)

    VRBO

    Luxury Designer Apartment | Patio | Gold Coast

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Summary: BRAND NEW APARTMENT IN THE HEART OF GOLD COAST! Enjoy your own luxury unit in Chicago's Gold Coast-the city's ...

    From $668 per night (USD)

    VRBO

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $310 per night (USD)

    Expedia

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in Rush & Division with balcony views over the city. It’ll ...

    From $310 per night (USD)

    Expedia

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $133 per night (USD)

    VRBO

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in Rush & Division with balcony views over the city. It’ll ...

    From $133 per night (USD)

    VRBO

    Details
  • Blueground | Streeterville, pool & gym, nr pier
    From $92 per night (USD)

    Expedia

    Blueground | Streeterville, pool & gym, nr pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    1

    Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...

    From $92 per night (USD)

    Expedia

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $248 per night (USD)

    VRBO

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this charming Streeterville furnished two bedroom ...

    From $248 per night (USD)

    VRBO

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $361 per night (USD)

    Expedia

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in Streeterville with balcony views over the city. It’ll b ...

    From $361 per night (USD)

    Expedia

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $167 per night (USD)

    VRBO

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...

    From $167 per night (USD)

    VRBO

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $114 per night (USD)

    Expedia

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...

    From $114 per night (USD)

    Expedia

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $245 per night (USD)

    VRBO

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this lovely two bedroom Blueground apartment. You’ll love coming h ...

    From $245 per night (USD)

    VRBO

    Details
  • 3 Tranquil Eco-friendly Rooms, Stylish Decor, Near River North Hotspots
    From $514 per night (USD)

    VRBO

    3 Tranquil Eco-friendly Rooms, Stylish Decor, Near River North Hotspots

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...

    From $514 per night (USD)

    VRBO

    Details
  • 2 Sleek Eco-friendly Rooms w/ Natural Furnishings in Vibrant River North
    From $342 per night (USD)

    VRBO

    2 Sleek Eco-friendly Rooms w/ Natural Furnishings in Vibrant River North

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...

    From $342 per night (USD)

    VRBO

    Details
  • Experience Comfort in Eco-friendly Room w/ Earth Tone Furniture
    From $215 per night (USD)

    VRBO

    Experience Comfort in Eco-friendly Room w/ Earth Tone Furniture

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...

    From $215 per night (USD)

    VRBO

    Details
  • Relaxing Eco-friendly Room w/ Modern Decor near River North Attractions
    From $174 per night (USD)

    VRBO

    Relaxing Eco-friendly Room w/ Modern Decor near River North Attractions

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...

    From $174 per night (USD)

    VRBO

    Details
  • Cozy Eco-friendly Room w/ Earth Tone Decor, Short Walk to River North Spots
    From $209 per night (USD)

    VRBO

    Cozy Eco-friendly Room w/ Earth Tone Decor, Short Walk to River North Spots

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...

    From $209 per night (USD)

    VRBO

    Details
  • Blueground | River North, pool & gym, nr Mile
    Click For Pricing

    VRBO

    Blueground | River North, pool & gym, nr Mile

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this lovely Near North furnished two bedroom apart ...

    Click For Pricing

    VRBO

    Details
  • Blueground | River North, balcony & pool, nr Pier
    From $252 per night (USD)

    Expedia

    Blueground | River North, balcony & pool, nr Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished two bedroom apar ...

    From $252 per night (USD)

    Expedia

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $150 per night (USD)

    VRBO

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...

    From $150 per night (USD)

    VRBO

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $112 per night (USD)

    Expedia

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...

    From $112 per night (USD)

    Expedia

    Details
  • Blueground | Streeterville, rooftop, pool, nr park
    From $125 per night (USD)

    VRBO

    Blueground | Streeterville, rooftop, pool, nr park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...

    From $125 per night (USD)

    VRBO

    Details
  • Blueground | Gold Coast, BBQ & gym, nr Hancock
    From $117 per night (USD)

    Expedia

    Blueground | Gold Coast, BBQ & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...

    From $117 per night (USD)

    Expedia

    Details
  • Blueground | River North, rooftop & pool, nr Mart
    From $204 per night (USD)

    VRBO

    Blueground | River North, rooftop & pool, nr Mart

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this roomy one bedroom Blueground apartment. You’ll love coming ho ...

    From $204 per night (USD)

    VRBO

    Details
  • Luxury Downtown 4BR | Exclusive Design PH
    From $2913 per night (USD)

    Expedia

    Luxury Downtown 4BR | Exclusive Design PH

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Summary: Elevate your Chicago experience in this breathtaking, luxury penthouse. Imagine stepping onto your expansive pr ...

    From $2913 per night (USD)

    Expedia

    Details
  • Blueground | Gold Coast, rooftop & gym, nr Hancock
    From $126 per night (USD)

    VRBO

    Blueground | Gold Coast, rooftop & gym, nr Hancock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished two bedroom a ...

    From $126 per night (USD)

    VRBO

    Details
  • Blueground | Gold Coast, BBQ & gym, nr Hancock
    From $129 per night (USD)

    Expedia

    Blueground | Gold Coast, BBQ & gym, nr Hancock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...

    From $129 per night (USD)

    Expedia

    Details
  • Blueground | River North, pool & gym, nr Mile
    Click For Pricing

    VRBO

    Blueground | River North, pool & gym, nr Mile

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...

    Click For Pricing

    VRBO

    Details
  • Blueground | River North, pool & gym, nr Mile
    From $121 per night (USD)

    Expedia

    Blueground | River North, pool & gym, nr Mile

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in Near North. It’ll be easy to simply show up and start l ...

    From $121 per night (USD)

    Expedia

    Details
  • Blueground | Streeterville, rooftop, pool, nr Pier
    From $216 per night (USD)

    VRBO

    Blueground | Streeterville, rooftop, pool, nr Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Streeterville furnished one bedroom ...

    From $216 per night (USD)

    VRBO

    Details
  • Blueground | The Loop, pool & w/d, nr park
    From $154 per night (USD)

    Expedia

    Blueground | The Loop, pool & w/d, nr park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Chicago Loop furnished one bedr ...

    From $154 per night (USD)

    Expedia

    Details
  • City View Smart, luxurious 1bd apartment - Downtown Chicago
    Click For Pricing

    VRBO

    City View Smart, luxurious 1bd apartment - Downtown Chicago

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    City View Smart, luxurious 1BD apartment with stunning Chicago skyline views, a personalized Pilates reformer, and centr ...

    Click For Pricing

    VRBO

    Details
  • Charming 2-bedroom condo with AC and WiFi in lakefront downtown Chicago
    Click For Pricing

    Expedia

    Charming 2-bedroom condo with AC and WiFi in lakefront downtown Chicago

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Unwind in Chicago at this charming condo. With 2 bedrooms featuring 2 queen beds, 2 bathrooms with a shower with body so ...

    Click For Pricing

    Expedia

    Details